(+)-3-O-(2'-methoxybenzyl)-5-O-(4'-methoxybenzyl)-conduritol B

Base Information

• Chemical Name: (+)-3-O-(2'-methoxybenzyl)-5-O-(4'-methoxybenzyl)-conduritol B
• CAS No.: 741256-78-0
• Molecular Formula: C₂₂H₂₆O₆
• Molecular Weight: 386.445
• Mol file: 741256-78-0.mol

Synonyms:(+)-3-O-(2'-methoxybenzyl)-5-O-(4'-methoxybenzyl)-conduritol B

Chemical Property of (+)-3-O-(2'-methoxybenzyl)-5-O-(4'-methoxybenzyl)-conduritol B

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-3-O-(2'-methoxybenzyl)-5-O-(4'-methoxybenzyl)-conduritol B

There total 5 articles about (+)-3-O-(2'-methoxybenzyl)-5-O-(4'-methoxybenzyl)-conduritol B which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

(3S,4R,5R,6S)-3-(2'-methoxybenzyloxy)-5-(4'-methoxybenzyloxy)-4,6-dihydro-octa-1,7-diene (741256-77-9) → (+)-3-O-(2'-methoxybenzyl)-5-O-(4'-methoxybenzyl)-conduritol B (741256-78-0)

Guidance literature:

With Grubbs catalyst first generation; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1248/cpb.52.727

Reference yield:

(3aR,5S,6S,6aR)-6-(4-methoxybenzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxole-5-carbaldehyde (82529-87-1) → (+)-3-O-(2'-methoxybenzyl)-5-O-(4'-methoxybenzyl)-conduritol B (741256-78-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: copper iodide; dimethyl sulfide / tetrahydrofuran / 0.08 h / -40 °C

1.2: 75 percent / CH₂Cl₂ / 3 h / 20 °C

2.1: NaH / dimethylformamide / 2 h / ice bath cooling

2.2: 98 percent / dimethylformamide / 20 °C

3.1: 78 percent / aq. H₂SO₄ / tetrahydrofuran / 30 h / 60 °C

4.1: n-BuLi / diethyl ether / 1.5 h / 20 °C

4.2: 75 percent / diethyl ether; tetrahydrofuran / 20 °C

5.1: 84 percent / benzylidene-bis(tricyclohexylphosphine)-dichlororuthenium / CH₂Cl₂ / 3 h / 20 °C

With copper(l) iodide; Grubbs catalyst first generation; n-butyllithium; dimethylsulfide; sulfuric acid; sodium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.52.727

Reference yield:

1,2-O-isopropylidene-3-O-(4'-methoxybenzyl)-5-C-vinyl-β-L-ido-pentafuranose (741256-59-7) → (+)-3-O-(2'-methoxybenzyl)-5-O-(4'-methoxybenzyl)-conduritol B (741256-78-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaH / dimethylformamide / 2 h / ice bath cooling

1.2: 98 percent / dimethylformamide / 20 °C

2.1: 78 percent / aq. H₂SO₄ / tetrahydrofuran / 30 h / 60 °C

3.1: n-BuLi / diethyl ether / 1.5 h / 20 °C

3.2: 75 percent / diethyl ether; tetrahydrofuran / 20 °C

4.1: 84 percent / benzylidene-bis(tricyclohexylphosphine)-dichlororuthenium / CH₂Cl₂ / 3 h / 20 °C

With Grubbs catalyst first generation; n-butyllithium; sulfuric acid; sodium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.52.727

upstream raw materials:

(3S,4R,5R,6S)-3-(2'-methoxybenzyloxy)-5-(4'-methoxybenzyloxy)-4,6-dihydro-octa-1,7-diene

(3aR,5S,6S,6aR)-6-(4-methoxybenzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxole-5-carbaldehyde

1,2-O-isopropylidene-3-O-(4'-methoxybenzyl)-5-C-vinyl-β-L-ido-pentafuranose

1,2-O-isopropylidene-3-O-(4'-methoxybenzyl)-5-O-(2'-methoxybenzyl)-5-C-vinyl-β-L-ido-pentafuranose

Downstream raw materials:

1-O-tetrahydropyranyl-2,3-O-dibenzyl-4,5-O-di(4'-methoxybenzyl)-6-O-(2'-methoxybenzyl)-D-myo-inositol

1-O-tetrahydropyranyl-3-O-benzoyl-4,5-O-di(4'-methoxybenzyl)-6-O-(2'-methoxybenzyl)-D-myo-inositol

2,3-O-dibenzyl-4,5-O-di(4'-methoxybenzyl)-6-O-(2'-methoxybenzyl)-D-myo-inositol

(+)-3-O-benzoyl-4,5-O-di(4'-methoxybenzyl)-6-O-(2'-methoxybenzyl)-D-myo-inositol